Electrophotocatalytic tri- or difluoromethylative cyclization of alkenes

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(10), P. 2482 - 2490

Published: Jan. 1, 2023

Photoelectrocatalysis is mild yet potent and this work unlocks the potential of unactivated alkenes for oxidant-free oxidative cyclization alkenes.

Language: Английский

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Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(7), P. 4199 - 4208

Published: Jan. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Language: Английский

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Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(33), P. 6659 - 6666

Published: Jan. 1, 2022

A selective polychloromethylation and halogenation reaction of alkynes via a radical addition/spirocyclization cascade sequence was developed, in which applying polyhaloalkanes as the precursor polyhalomethyl halogen radicals.

Language: Английский

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Organic photoredox catalytic radical sulfonamidation/cyclization of unactivated alkenes towards polycyclic quinazolinones

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(22), P. 6290 - 6294

Published: Jan. 1, 2022

The synthesis of sulfonamidylated polycyclic quinazolinones was developed via visible-light-induced radical sulfonamidation/cyclization unactivated alkenes using 4CzIPN as the photocatalyst.

Language: Английский

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Metal-Free Photoinduced Hydrocyclization of Unactivated Alkenes toward Ring-Fused Quinazolin-4(3H)-ones via Intermolecular Hydrogen Atom Transfer

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1683 - 1688

Published: March 8, 2023

A visible-light-induced hydrocyclization of unactivated alkenes was developed using 3CzClIPN as the photocatalyst to generate substituted α-methyldeoxyvasicinones and α-methylmackinazolinones in moderate good yields. An intermolecular hydrogen atom transfer with THF source involved. Mechanism studies indicated that intramolecular addition situ formed aminal radical alkene generated polycyclic quinazolinone.

Language: Английский

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Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Language: Английский

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Cu-Catalyzed Relay Functionalization of Alkenes: Diverse Synthesis of Diazidated Quinazolinones and Polycyclic Imidazoles

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

A Cu-catalyzed relay process for the preparation of diazidated quinazolinone and polycyclic imidazole derivatives in which readily available alkene-tethered substrates undergo an addition/cyclization/C(sp3)–H functionalization alkene sequences with high efficiency is described. Various functionalized N-heteropolycyclic compounds were prepared good yields a broad substrate scope. Moreover, direct azidation α-C(sp3)–H bond corresponding N-heterocycles has been demonstrated on basis mechanistic studies, provide alternative late-stage approach derivatization N-heterocyclic scaffolds.

Language: Английский

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Trichloromethyl‐Radical‐Initiated Three‐Component Reaction of Alkenes with CHCl₃ and Quinoxalinones

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(5), P. 687 - 692

Published: Feb. 8, 2023

Abstract An iron(II)‐catalyzed three‐component reaction was developed for the construction of trichloromethylated 3‐benzylquinoxalin‐2(1 H )‐ones. This conducted through trichloromethylation alkenes with quinoxalin‐2(1 )‐ones using commercially available chloroform as trichloromethyl radical source, which provided a convenient approach toward magnified image

Language: Английский

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Photocatalytic cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones for the construction of quinoxalino[2,1-b]quinazolinones

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(18), P. 2556 - 2559

Published: Jan. 1, 2024

3-(2-Isocyanophenyl)quinazolin-4(3 H )-ones were designed and synthesized as new building units for the construction of novel quinoxalino[2,1- b ]quinazolinones under mild, photocatalytic metal-free conditions.

Language: Английский

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(NH₄)₂S₂O₈ promoted tandem radical cyclization of quinazolin-4(3H)-ones with oxamic acids for the construction of fused quinazolinones under metal-free conditions

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(11), P. 2241 - 2251

Published: Jan. 1, 2024

A novel cascade radical addition/cyclization reaction of non-activated olefins and oxamic acids has been proposed.

Language: Английский

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